Boron and aluminum compounds in electronic components

Abstract

The present invention relates to the use of boron and aluminum compounds in electronics, in particular as electron transport material, as host material of the emission layer and as hole blocking material, in each case in phosphorescent OLEDs, and also to layers produced therefrom in phosphorescent OLEDs.

1. A host material of an emission layer in phosphorescent OLEDs which comprises at least one of the compound which comprises a substituted boron compound of the formula (I) 
       
         
           
           
               
               
           
         
       
       wherein
 Aryl 1,3-terphenyl, tetraphenyl, fluorene, phenanthrene, 1,3,5-triphenylbenzene, perylene, chrysene, trypticene, [2.2]paracyclophane, ferrocene, pyridine, pyridazine, 4,5-benzopyridazine, pyrimidine, pyrazine, 1,3,5-triazine, pyrrole, indole, 1,2,5-oxadizole, 1,3,4-oxadiazole, 2,2′-diazabiphenyl, 4,4′-diazabiphenyl, quinoline, carbazole, 5,10H-dihydrophenazine, 10H-phenoxazine, xanthene or 9-acridine; 
 Ar 1  and Ar 2  are identical or different on each occurrence and are each phenyl, 1-naphthyl, 2-naphthyl, 1-anthracenyl, 2-anthracenyl, 9-anthracenyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 3-pyridazinyl, 4-pyridazinyl, 2-quinolinyl, 3-quinolinyl, 4-quinolinyl, 5-quinolinyl, 6-quinolinyl, 7-quinolinyl, 8-quinolinyl, 2-pyrrolyl, 3-pyrrolyl, 2-furanyl, 3-furanyl or 2-(1,3,4-oxadiazol)yl; 
 Q1, Q2 and Q3 are identical or different on each occurrence and are each CN, F, Cl or a straight-chain or branched or cyclic alkyl or alkoxy group which has from 1 to 20 carbon atoms and in which one or more nonadjacent CH 2  groups is optionally replaced by —O—, —S—, —CO—, —COO—, —O—CO—, —NR 1 —, —(NR 2 R 3 ) + A −  or —CONR 4 — and one or more H atoms is optionally replaced by F, or an aryl or heteroaryl group which has from 4 to 14 carbon atoms and is optionally substituted by one or more CN, F, Cl or a straight-chain or branched or cyclic alkyl or alkoxy group which has from 1 to 20 carbon atoms and in which one or more nonadjacent CH 2  groups is optionally replaced by —O—, —S—, —CO—, —COO—, —O—CO—, —NR 1 —, —(NR 2 R 3 ) + A −  or —CONR 4 — and one or more H atoms is optionally replaced by F; A −  is a singly charged anion or its equivalent; 
 R 1 , R 2 , R 3  and R 4  are identical or different and are each H or an aliphatic or aromatic hydrocarbon radical having from 1 to 20 carbon atoms or a corresponding fluoroalkyl or fluoroalkoxy radical; 
 m are identical or different and are each 0, 1, 2, 3, 4 or 5; 
 x are identical or different and are each 0, 1, 2, 3, 4 or 5; 
 y are identical or different and are each 0, 1, 2, 3, 4 or 5; 
 n is 2; 
 Z is boron. 
 
     
     
       2. The material as claimed in  claim 1 , wherein the radicals Ar 1  and Ar 2  are identical or different and are each phenyl, 1-naphthyl or 2-naphthyl. 
     
     
       3. The material as claimed in  claim 1 , wherein R 1,  R 2,  R 3  and R 4  if present are identical or different and are each H or an aliphatic or aromatic hydrocarbon radical having from 1 to 20 carbon atoms. 
     
     
       4. A host material of an emission layer in phosphorescent OLEDs which comprises at least one of the compound which comprises a substituted aluminum compound aluminum compounds of the formula (I) 
       
         
           
           
               
               
           
         
       
       wherein
 Aryl is a carbocyclic or heterocyclic aromatic ring or ring system having from 2 to 60 carbon atoms or a plurality of aromatic rings which each have from 6 to 14 carbon atoms and are joined to one another via a conjugated or nonconjugated linkage or via one or more metal atoms (sandwich complex); 
 Ar 1  and Ar 2  are identical or different on each occurrence and are each phenyl, 1-naphthyl, 2-naphthyl, 1-anthracenyl, 2-anthracenyl, 9-anthracenyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 3-pyridazinyl, 4-pyridazinyl, 2-quinolinyl, 3-quinolinyl, 4-quinolinyl, 5-quinolinyl, 6-quinolinyl, 7-quinolinyl, 8-quinolinyl, 2-pyrrolyl, 3-pyrrolyl, 2-furanyl, 3-furanyl or 2-(1,3,4-oxadiazol)yl; 
 Q1, Q2 and Q3 are identical or different on each occurrence and are each CN, F, Cl or a straight-chain or branched or cyclic alkyl or alkoxy group which has from 1 to 20 carbon atoms and in which one or more nonadjacent CH 2  groups is optionally replaced by —O—, —S—, —CO—, —COO—, —O—CO—, —NR 1 —, —(NR 2 R 3 ) + A − or —CONR   4 — and one or more H atoms is optionally replaced by F, or an aryl or heteroaryl group which has from 4 to 14 carbon atoms and is optionally substituted by one or more CN, F, Cl or a straight-chain or branched or cyclic alkyl or alkoxy group which has from 1 to 20 carbon atoms and in which one or more nonadjacent CH 2  groups is optionally replaced by —O—, —S—, —CO—, —COO—, —O—CO—, —NR 1 —, —(NR 2 R 3 ) + A − or —CONR   4 — and one or more H atoms is optionally replaced by F; 
 A −  is a singly charged anion or its equivalent; 
 R 1 , R 2 , R 3  and R 4  are identical or different and are each H or an aliphatic or aromatic hydrocarbon radical having from 1 to 20 carbon atoms or a corresponding fluoroalkyl or fluoroalkoxy radical; 
 m are identical or different and arc each 0, 1, 2, 3, 4 or 5; 
 x are identical or different and arc each 0, 1, 2, 3, 4 or 5; 
 y are identical or different and are each 0, 1, 2, 3, 4 or 5; 
 n is 2, 3, 4, 5 or 6; 
 Z is aluminum. 
 
     
     
       5. The material as claimed in  claim 4 , wherein Aryl is benzene, biphenyl, 1,2-terphenyl 1,3-terphenyl, 1,4-terphenyl, tetraphenyl, naphthalene, fluorene, phenanthrene, 1,3,5-triphenylbenzene, pyrene, perylene, chrysene, trypticene, [2.2]paracyclophane, ferrocene, pyridine, pyridazine, 4,5-benzopyridazine, pyrimidine, pyrazine, 1,3,5-triazine, pyrrole, indole, 1,2,5-oxadizole, 1,3,4-oxadiazole, 2,2′- diazabiphenyl, 4,4′-diazabiphenyl, quinoline, carbazole, 5,10H-dihydrophenazine, 10H-phenoxazine, xanthene or 9-acridine. 
     
     
       6. The material as claimed in  claim 4 , wherein Ar 1  and Ar 2  are identical or different and are each phenyl, 1-naphthyl or 2-naphthyl. 
     
     
       7. The material as claimed in  claim 5 , wherein Ar 1  and Ar 2  are identical or different and are each phenyl, 1-naphthyl or 2-naphthyl. 
     
     
       8. The material as claimed in  claim 4 , wherein R 1 , R 2 , R 3  and R 4    
       if present are identical or different and are each H or an aliphatic or aromatic hydrocarbon radical having from 1 to 20 carbon atoms. 
     
     
       9. The material as claimed in  claim 6 , wherein R 1 , R 2 , R 3  and R 4  if present are identical or different and are each H or an aliphatic or aromatic hydrocarbon radical having from 1 to 20 carbon atoms. 
     
     
       10. A host material of an emission layer in phosphorescent OLEDs which comprises at least one of the compound which comprises a substituted boron compound compounds of the formula (I) 
       
         
           
           
               
               
           
         
       
       wherein
 Aryl benzene, biphenyl, 1,2-terphenyl 1,3-terphenyl, 1,4-terphenyl, tetraphenyl, naphthalene, fluorene, phenanthrene, 1,3,5-triphenylbenzene, pyrene, perylene, chrysene, trypticene, [2.2]paracyclophane, ferrocene, pyridine, pyridazine, 4,5-benzopyridazine, pyrimidine, pyrazine, 1,3,5-triazine, pyrrole, indole, 1,2,5-oxadizole, 1,3,4-oxadiazole, 2,2′-diazabiphenyl, 4,4′-diazabiphenyl, quinoline, carbazole, 5,10H-dihydrophenazine, 10H-phenoxazine, xanthene or 9-acridine; 
 Ar 1  and Ar 2  are identical or different on each occurrence and are each phenyl, 1-naphthyl, 2-naphthyl, 1-anthracenyl, 2-anthracenyl, 9-anthracenyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 3-pyridazinyl, 4-pyridazinyl, 2-quinolinyl, 3-quinolinyl, 4-quinolinyl, 5-quinolinyl, 6-quinolinyl, 7-quinolinyl, 8-quinolinyl, 2-pyrrolyl, 3-pyrrolyl, 2-furanyl, 3-furanyl or 2-(1,3,4-oxadiazol)yl; 
 Q1, Q2 and Q3 are identical or different on each occurrence and are each CN, F, Cl or a straight-chain or branched or cyclic alkyl or alkoxy group which has from 1 to 20 carbon atoms and in which one or more nonadjacent CH 2  groups is optionally replaced by —O—, —S—, —CO—, —COO—, —O—CO—, —NR 1 —, —(NR 2 R 3 ) + A −  or —CONR 4 — and one or more H atoms is optionally replaced by F, or an aryl or heteroaryl group which has from 4 to 14 carbon atoms and is optionally substituted by one or more CN, F, Cl or a straight-chain or branched or cyclic alkyl or alkoxy group which has from 1 to 20 carbon atoms and in which one or more nonadjacent CH 2  groups is optionally replaced by —O—, —S—, —CO—, —COO—, —O—CO—, —NR 1 —, —(NR 2 R 3 ) + A −  or —CONR 4 — and one or more H atoms is optionally replaced by F; 
 A − is a singly charged anion or its equivalent; 
 R 1 , R 2 , R 3  and R 4  are identical or different and are each H or an aliphatic or aromatic hydrocarbon radical having from 1 to 20 carbon atoms or a corresponding fluoroalkyl or fluoroalkoxy radical; 
 m are identical or different and are each 0, 1, 2, 3, 4 or 5; 
 x are identical or different and are each 0, 1, 2, 4 or 5; 
 y are identical or different and are each 0, 1, 2, 4 or 5; 
 n is 2; 
 Z is boron. 
 
     
     
       11. The material as claimed in  claim 10 , wherein the radicals Ar 1  and Ar 2  are identical or different and are each phenyl, 1-naphthyl or 2-naphthyl. 
     
     
       12. The material as claimed in  claim 10 , wherein R 1,  R 2 , R 3  and R 4  are identical or different and are each H or an aliphatic or aromatic hydrocarbon radical having from 1 to 20 carbon atoms.